


Round One

by spacegayofficial



Category: Kingsman (Movies)
Genre: F/M, First Kiss, In This House We Use Lube For PiV Sex, Jack is a gentleman, Oral Sex, Penis In Vagina Sex, first kiss and first time having sex all wrapped up into one! how about that!, virgin!reader
Language: English
Status: Completed
Published: 2020-08-26
Updated: 2020-08-26
Packaged: 2021-03-06 23:28:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,122
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26127259
Author URL: https://archiveofourown.org/users/spacegayofficial/pseuds/spacegayofficial
Summary: After harboring a little bit of a crush on Whiskey for a while, you finally find yourself alone with him, at his place no less. He makes a move, and you have a bit of a confession.
Relationships: Jack | Whiskey (Kingsman)/Reader
Comments: 2
Kudos: 88





	Round One

Honestly, how you got into this situation in the first place is beyond you. You wouldn’t necessarily describe yourself as particularly flirtatious or outgoing, and how you caught the eye of a man who seemed to be the living definition of “flirtatious and outgoing” was still a mystery. But you definitely weren’t complaining. Well, not exactly, anyway, but you were… nervous.

Your coworker, Agent Whiskey, had always come across to you as somewhat of a… playboy, maybe, and at first, you were absolutely convinced he was someone you should never, ever get involved with. Not that you were in some big rush to get involved with anyone as it was. You’d tried to date, before, but no one felt… right. Nothing ever clicked for you, and before you knew it, you were surrounded by friends who had settled down and you hadn’t so much as kissed someone. You reminded yourself that life isn’t a race, and that it’s okay, that you’ll end up where you need to be when you need to be there, but still, you couldn’t shake the feeling that somehow you had aged out of your chance for a relationship. But, then you went against your own advice of avoiding Whiskey, and things  _ did _ click, and things  _ did _ feel right, but you found yourself with a new host of doubts. Did he feel the same? Were you just another one night stand? Would he change his mind on everything when he found out you’d never had sex? Hadn’t even kissed anyone?

Still, though, here you were, sitting in his living room, drinking, flirting, laughing, and enjoying yourself, and the tension was there and it was going to snap any minute and you didn’t know what you were going to do when it did. You were sitting fairly close together on the couch, and Jack laughed at something you said and put a hand on your thigh. This was definitely a move, you thought, and while it was nice, you sort of tensed up before you even realized you were reacting to it. He lifted his hand a bit, and furrowed his brow.

“I apologize, darlin’, didn’t mean to overstep, I just thought…” Jack started, clearly a little confused.

“What? No! No, you didn’t overstep, I just, um,” you started. You took a sip of your drink, your eyes falling to your hands as you fidgeted a little bit in your lap. “I, uh… This is all new territory for me. Dating… never worked out for me, and I never got past the first date most of the time, so I uh… I haven’t…” You paused, biting your lip, wondering if there was a tactful way to say you had no idea what you were doing.

Jack hummed quietly in understanding and you looked back up at him. “I believe I know where you’re goin’ with that, sugar, and that is completely fine,” he said, “but I don’t want you to feel pressured into doin’ anythin’ if it’s gonna make you uncomfortable.”

Honestly, despite your initial “don’t get involved with Whiskey” policy, the thought had crossed your mind that if you were going to have anyone in the world be your first time, for either kissing or sex, it probably wouldn’t be a bad idea to have him. He’s experienced, he knows what he’s doing, and despite his outgoing brashness, he was very much a gentleman. You could definitely learn a thing or two from him. You didn’t feel pressured or uncomfortable at all, you were just concerned he wouldn’t want to be that first time.

“You’re not making me uncomfortable or pressuring me or anything,” you assured him. “I promise. I just… Jack, I haven’t even had my first kiss, and I know some guys are weird about people with no experience and, um… yeah. You know.”

Jack smiled at you softly. “I don’t mind,” he told you. “But  _ I _ know that some folks are choosy about their first times, and I just wanna make sure this is what you want.”

You smiled back at him, and excitement started to bubble up in you. He was okay with this. Oh man. “Yeah. It is what I want,” you responded, nodding a bit. You eyed his lips for a moment, and then back at his eyes, patiently waiting some sort of direction.

“May I?” Jack asked, still smiling, as he brought a hand up to your cheek and leaned in just a bit.

You nodded. “Yeah,” you responded quietly, buzzing with anticipation.

He closed the gap between you, gently pressing his lips to yours. You followed your instincts, and pressed back. Jack took small steps to up the intensity as you kissed, first taking your bottom lip between his, then nibbling gently, then swiping his tongue into your mouth. You followed his lead, and honestly, you weren’t too bad at this, if you were being honest. Better than you thought you would be with absolutely no other reference point. Along those same lines, this felt nice. Being this close to someone, it felt… tingly, almost, and warm. It was like the sound of a fuse burning down to a firework. Before long, and before you really even registered it, he had pulled you into his lap so you were straddling him. You had one hand on his shoulder, the other playing with the hair on the back of his neck. Eventually you parted for air, and you looked at him, a little bit dazed, and laughed quietly.

“You’re a natural at this,” Jack said, kissing you again quickly. You could keep doing that for hours.

“Really? Well, I mean, I have a very good teacher,” you responded, and he chucked quietly.

Jack leaned in again for a slightly longer, but still fairly brief, kiss. His hands were on your hips, his fingers edging up under the hem of your shirt. You shifted a bit in his lap, and you could feel him growing hard and pressing up into your core. You gasped quietly at the change in pressure, and he responded by pressing a quick kiss to your jawline.

“As appealin’ as the idea of takin’ you right here is,” he started, his voice quieter, raspier now, “I don’t think that’ll do your first time any justice. Let me take you to bed, sugar.” He nipped your jaw, and you barely got out a full nod before he was standing, his hands grabbing on to your thighs to pick you up. You gasped in surprise, wrapping your arms around Jack’s neck to keep yourself upright, and wrapping your legs around him to assist in that task.

After a few short steps, he set you down gently on the bed, still sitting up, and kissed you again. His hands drifted under your shirt, pushing it up some. He pulled away from the kiss just enough to speak. “You tell me if I’m goin’ too fast or you wanna stop, alright?” he said quietly, genuine concern in his voice. He really wanted to do this right by you.

“Of course,” you agreed, just as quietly, smiling softly.

Jack smiled back at you, his hands moving down to grab the hem of your shirt in earnest. “May I?” he asked again. You nodded again, letting go of his neck and letting him lift your shirt up and off of you. In the same motion he unclasped your bra, and tossed both garments on the floor. He leaned down and kissed your neck, then across your shoulder, and back in across your collarbone. His hands skimmed over your sides again, gently pushing you back further onto the bed. You scooted back, closer to the middle, and he followed close behind, kissing your sternum and down your belly almost reverently; none of his kisses would leave visible marks, and he seemed in awe of your body, like being able to see it and touch it was a great honor. In his opinion, it sort of was; while he of all people knew better than to attach a moral value to whether or not someone had had sex, he knew that it was a pretty big deal that you were letting him be your first time, letting him be the first person to taste you, to feel you, to make you come undone by their hand. He’d be lying if he said it didn’t excite him.

Your fingers found his hair, combing through it gently as his fingers worked on unbuttoning your pants. He looked up at you as if to ask the same question as before, and you nodded again. He pulled your pants down, and you pushed your hips up off the bed to help with that endeavor. Those joined your other clothes on the floor, and Jack went back to kissing over your skin and working his way down your body. His lips grazed the skin on your hip, the scratch of his mustache sending shivers down your spine. He moved to start kissing your thighs, all over them, spending plenty of time on your inner thighs which was starting to drive you a little crazy. His mouth on you felt incredible as it was, and you couldn’t even begin to imagine how good it would feel once he took your panties (which you were sure had a pretty sizable wet spot on them at this point) off and put it there. A quiet moan escaped your lips as he nibbled gently on the inside of your thigh.

He hooked his fingers in the waistband of your panties and gently pulled them down, and you lifted your hips again to let him take them off of you. Once they were off, he gently took your thighs in his hands, pushing one out and away and the other over his shoulder. Your fingers found his hair again, carding through it as he adjusted between your legs. He gently rubbed two fingers over you, spreading you out for him even further, and you sighed. He hummed a bit, just looking at you for now.

“What a pretty sight,” Jack mused. He brushed his fingers over your clit, and you gasped, short of a whine, your hips jerking just a bit under his touch. “You just let me take care of you.” With that, you felt his tongue lick a wide, slow stripe up from your entrance to your clit, and you moaned. It was decidedly a new feeling, but it was very good, and you wanted more. Your grip in his hair tightened, and you felt the rumbles of a small laugh come from him. He did it again, then latched his lips to your clit, and sucked gently. You cried out again. You were somewhat overwhelmed by the amount of new sensations, here, but you were far from trying to tap out. That being said, you were afraid you weren’t going to last very long if Jack kept this up.

As if he could read your thoughts, Jack left your clit alone for a few moments to work a finger into you gently, watching as you took him. A satisfied hum came from him as you clenched around him a bit.

“Relax, baby, relax for me,” he cooed, his free hand resting on your belly, his thumb stroking your skin. He pressed a kiss to the inside of your thigh again as you did what he asked and focused on relaxing. His single finger in you worked in and out until he was sure you were used to its presence, then he began to work in his second finger. His fingers were definitely thicker than yours, by quite a bit, and the stretch you were feeling was amazing. Not at all painful, he clearly knew what he was doing, taking his time to make sure you felt good.

You let out another moan as he crooked his fingers inside you, stretching you even further for him in a different way. His fingers rubbed along your walls, in search of something. Something that made you clench around him and groan when he finally pressed his fingers into it.

“Oh my god, Jack,” you gasped, gripping into his hair even harder, instinctively trying to pull his face closer to you. You heard Jack chuckle again.

“Just you wait, darlin’,” he said, giving in to the tugging at his hair and closing the gap between you and his face once more. His tongue flicked over your clit and you gasped, your hips bucking into the sensation. He slowly worked his way up from there, a few more flicks, then more firm licks varying in direction, then finally, after what felt like eons, he once again drew your clit into his mouth and sucked. The entire time, his fingers in you were rubbing against that sensitive spot. You were moaning, whimpering, whining as he went, noises you were fairly certain you’d never made before. Jack was making you feel absolutely incredible, any nervousness from before melting away into nothing. You never wanted this to stop; you were sure it was partially the novelty, but some other part of you was fairly convinced this was going to be the best oral you’d ever get. He wasn’t rushed to get done, didn’t seem like he felt obligated to this, and, if the occasional groan and grunt coming from him was any indication, he seemed to be enjoying this almost as much as you were.

Jack definitely didn’t seem to be in any hurry to get you to climax, and was taking his sweet time increasing his intensity the tiniest bit at a time, including how fast or how hard he was rubbing his fingers along your walls, which was making you practically writhe underneath him. His name was escaping your lips with more frequency, though, as he did get you worked up, and you were starting to feel that familiar tightening (although it had an odd sense of newness since it wasn’t you in control this time) approaching a point where it would break.

“Jack, Jack, I’m so fucking close,” you gasped out, your eyes screwing shut as you barrelled towards that edge.

He replaced his tongue momentarily with his thumb. “C’mon, baby, cum for me,” Jack said, barely above a whisper, before returning his lips to your clit and sucking hard. He moaned around you, which did you in.

If you were more aware of your surroundings, you might be a little afraid you were pulling too hard on Jack’s hair. Your legs closed around his head, and your hips grinded up into his face with your heels digging into his back, unwilling to give up any miniscule bit of friction as you reached a high infinitely better than anything you’d ever given yourself. You were chanting Jack’s name like a prayer as he coaxed everything he could out of you, bringing you down gently but still lapping up every bit of your essence. Once you let his head go from between your legs, and you were twitching and trying to pull his head away by your grip in his hair, he let you go, slipping his fingers out of you and leaning back. He gave you a clear view as he licked and sucked his fingers clean, moaning in satisfaction as he did.

Jack grinned back at you, impressed at how disheveled you already looked. “Sweet as honey,” he said, before climbing over you and pressing his lips to yours again. He swiped his tongue into your mouth, and you tasted yourself on him, which made you moan quietly. Your hands found their way back into his hair, pulling him against you gently as you kissed. You followed your gut, which hasn’t steered you wrong too frequently in your lifetime, and reached for the hem of his shirt and pulled it up. Jack pulled away from the kiss, much to your dismay, to take his shirt off, giving you a good look at his toned arms and wide shoulders and chest and that little hint of a belly that was starting to show. You leaned up a little bit to follow, to get closer, and as you reached for the button on his jeans, you noticed just how worked up he’d gotten being between your legs.

Your eyes flicked up to him, almost searching for permission, and he just nodded slightly, smiling warmly. You unclasped the button on his jeans and he made a small noise of relief, and you pushed them down over his hips. His cock was straining against the stretchier fabric of his boxers, and there was a pretty substantial wet spot where the tip was. You reached forward and ran your hand over it, and Jack hissed, grabbing your hand and pressing it against him a bit harder.

“Sweetheart, why don’t we save that for a little later,” he ground out, taking your hand away from him to push his boxers out of the way, tossing his bottoms on the floor with everything else.

Okay, so now you were a little nervous for another reason. He was quite well endowed, and you were a bit intimidated by that. But, unsurprisingly given how he was treating you the entire evening, Jack was well aware of this potential speed bump and was prepared for it. He leaned back down over you, kissing you again, and reached for his bedside table. He grabbed something out of the drawer, and you heard something click. He leaned back again, and you registered he had a bottle of lube and was squeezing a generous amount into his hand before closing the bottle again and stroking himself to spread it around. The excess he spread on your pussy, making you gasp with the temperature difference.

Jack then gently grabbed one of your hands and, as he hovered over you once again, wrapped it around his cock, brushing his tip through your slick folds. He groaned quietly. “Take your time,” he told you, and you nodded slightly, lining him up with your entrance. Doing exactly what he said, you ever so slowly pulled him forward, pressing into you. You were thankful you were wet as it was, and the lube helped considerably; you could enjoy the stretch rather than worry about him hurting you or it pulling uncomfortably. And stretch you he did, his cock much thicker than his fingers. It made your eyes roll back slightly, a moan falling from your lips as the ridge of the head pushed past your opening. Jack moaned as your wet heat enveloped him, and he was once again reminded how lucky he was to be the first to experience this.

After a few excruciating minutes of pulling him forward and letting yourself adjust to the stretch, full of moaning from both of you as he slid in deeper and deeper, he was finally seated as deep as he could go, and he was rubbing right against that same sensitive spot inside you as his fingers were before. You looked up into his eyes, and he smiled down at you, kissing you again. He moved his hips experimentally, more a grind than a thrust, and you gasped against his lips, your hips moving up a bit to meet his. You felt full, and it was magnificent; another very new, very good feeling.

“Doin’ alright?” he asked quietly, nipping at your bottom lip gently.

“Fantastic,” you gasped, and you both moaned a bit as your walls fluttered around him. “Please move, Jack.”

He did not need to be asked twice, and especially with not how good your voice sounded saying his name right now. He started moving his hips, slow and shallow at first, again letting you adjust to the new sensation of him dragging against your walls. One of his hands dropped between you, his thumb pressing on your sensitive bundle of nerves, making your hips buck and your pussy clench around him. You both moaned yet again, you at the sensation of your oversensitive clit being stimulated again, him at how spectacular you felt around him.

“Christ, darlin’, you’re so fuckin’ tight,” he groaned, his forehead resting against yours. “Feel so good around me, baby, wanna stay right here forever.”

You moaned and clenched around him again at the sound of his voice, the raspy tone and his accent sending a new wave of pleasure right to your core that you weren’t exactly expecting but you also weren’t necessarily surprised by.

Much the same way as he was working you up slowly with his mouth, he worked you up slowly with his cock and his fingers working your clit. He kissed you and nipped at your lips and kissed down to your jaw and neck as he worked, adding to the overall sensations. You were in heaven, practically boneless beneath him other than your arms loosely around his neck, your fingers playing with his hair, letting yourself get lost in the pleasure of all of this. You couldn’t remember why you were nervous about anything at this point.

Jack increased his pace until he settled into a fairly quick, steady rhythm that was getting you to another orgasm fast. He could tell, too, as he sped up his thumb rubbing your clit and pulled away just enough to look at you.

“One more, sugar, one more for me,” he panted, dipping down to kiss you again. “Please, I wanna see your beautiful face when I make you cum, angel, let go for me.”

Jack’s pleas made you moan again and nod slightly, looking up at him as you once again crested, even more powerfully than before. Your back arched under him, pressing him somehow further into you. You thought he was saying something to you, but your ears were ringing and you couldn’t process whatever it was. You pulsed and fluttered around his cock, and he moaned in your ear, his head dropping to your shoulder. He nibbled there gently as he drew out your orgasm to a satisfying completion.

He then grunted, his hips stuttering as he hit his own climax. You felt him twitch and spill into you, yet another new but very good sensation. He practically collapsed on top of you, lazily pressing kisses to your skin as he came down from his high, his hips occasionally rutting into you.

You ran your fingers through Jack’s hair again, and he pushed himself up to kiss you. You looked at him as he pulled away, still a bit dazed from how intense everything was. You smiled, though, and laughed a little bit.

“Jack, that was…” you started, shaking your head a little bit, “so much better than I thought it would be it’s crazy.”

Jack grinned back at you, pressing a kiss to your forehead. “Good. I aim to please,” he responded. You both hummed quietly as he pulled out, and you gasped once again at the feeling of his cum leaking out of you. Jack leaned back on his knees and smirked as he saw what you were feeling, then looked back up to you. “You’re a goddamn dream, sweetheart.”

You felt your cheeks heat up a little bit, and you laughed again. “You’re the dream, making my first time better than anything else I’ll ever get,” you said, feigning irritation.

Jack’s expression changed to one of slight confusion. “Hang on now, I haven’t pulled every trick outta my bag yet,” he said. He looked you over again, licking his lips slowly. “At least, I was plannin’ on showin’ you a little more if you’re interested in a round two. Or three. Or…” he trailed off.

You blinked up at him. Your concerns about him feeling the same were also dashed. “Wait, you mean you--this wasn’t just--” you stuttered out, then paused, taking a deep breath. “I guess I wasn’t expecting this to be more than a… one night stand, or something.”

Jack shook his head, almost in disbelief. “Honey, I was hopin’ this would be much more than that,” he confessed. “I’ve been tryin’ to get you to go out with me or somethin’ for weeks.”

When he mentioned it, you realized that all those times he invited you out for drinks or to grab dinner after work wasn’t to hang out with your coworkers, he was trying to get you out on a date. “Oh, my god, Jack, I’m so oblivious,” you groaned, covering your face with your hands.

He laughed quietly and climbed over you again, moving your hands from your face and kissing you again, softer this time. “Well, tell you what, I can think of a few ways you can make it up to me.”

**Author's Note:**

> Thanks for reading!! Come hang out n say hi over at spacegayofficial on tumblr!!


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